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Phenol
pKa = 9-11
Acidic under physiological conditions
Sulfonamide
pKa = 9-10
Acidic under physiological conditions
Imide
pKa = 9-10
Acidic under physiological conditions
Alkylthiol
pKa = 10-11
Acidic under physiological conditions
Thiophenol
pKa = 6-7
Acidic under physiological conditions
N-Arylsulfonamide
pKa = 6-7
Acidic under physiological conditions
(N-)Acylsulfonamide
pKa = 5-6
Acidic under physiological conditions
Alkylcarboxylic Acid
pKa = 5-6
Acidic under physiological conditions
Arylcarboxylic Acid
pKa = 4-5
Acidic under physiological conditions
Sulfonic Acid
pKa = 0-1
Acidic under physiological conditions
Imine
pKa =3-4
Basic under physiological conditions
Arylamine
pKa = 4-5
Basic under physiological conditions
Pyridines
pKa = 5-6
Basic under physiological conditions
Alkylamines
pKa = 9-10 (primary), 10-11 (secondary)
Basic under physiological conditions
Amidine
pKa = 10-11
Basic under physiological conditions
Guanidine
pKa = 12-13
Basic under physiological conditions
Alkyl Alcohol
pKa =
__ under physiological conditions
Ether
Neutral
Ester
Neutral
Sulfonate Ester
Neutral
Amide
Neutral
Thioether
Neutral
Aldehyde
Neutral
Sulfoxide
Neutral
Nitrile
Neutral
Diarylamine
Neutral
Ketone
Neutral
Sulfone
Neutral
Carbamate
Neutral
Amine Oxide
Permanently charged across pH range
Quaternary ammonium
Permanently charged across pH range